KR20010033372A - Substituted guanidine derivatives - Google Patents

Abstract

The present invention relates to novel guanidine derivatives of the general formula (I)

Where

R ¹ is a heteroatom ring member containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms (where the number of heteroatoms is 1, 2, 3 or 4), Halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkyl Thio, alkenylthio, halogenoalkenylthio, alkynylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, arylthio, 5- or 6-membered heterocyclic group optionally substituted by arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and / or alkoxycarbonyl,

R ² represents hydrogen or alkyl,

R ³ represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ ,

From here,

R ⁴ , R ⁵ and R ⁶ are independently of each other alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkynyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl, or in each case optionally substituted phenyl Or benzyl,

R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, or in each case optionally substituted phenyl or benzyl,

R ⁹ represents alkyl or optionally substituted phenyl,

A represents a group -CH ₂ CH ₂ -,-(CH ₂ ) ₃ -or -CH = CH-,

Z represents cyano or nitro,

Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen,

R ¹ is , R ² is H, R ³ is OCH ₃ , A is -CH ₂ CH _2- , and the compound of general formula (I) wherein Z is NO ₂ is excluded.

Compounds of formula (I) are provided to control animal pests.

Description

Substituted guanidine derivatives

The present invention relates to novel guanidine derivatives, methods for their preparation and their use for controlling animal pests.

It is already known that certain heterocyclic compounds are pesticidal (see for example EP-A 0 192 060, EP-A 0 277 317, CA 125, 188 277; 121, 255 796; 121, 157 642 See literature).

However, the activity and / or activity spectrum of these compounds is not very satisfactory in all fields of use, especially when the application rates and concentrations are low.

Accordingly, the present invention provides novel guanidine derivatives of the general formula (I):

Where

R ¹ is a heteroatom ring member containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms (where the number of heteroatoms is 1, 2, 3 or 4), Halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkyl Thio, alkenylthio, halogenoalkenylthio, alkynylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, arylthio, A 5- or 6-membered heterocyclic group optionally substituted by arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and / or alkoxycarbonyl ,

R ² represents hydrogen or alkyl,

R ³ represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ ,

From here,

R ⁴ , R ⁵ and R ⁶ are independently of each other alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkynyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl, or in each case optionally substituted phenyl Or benzyl,

R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, or in each case optionally substituted phenyl or benzyl,

R ⁹ represents alkyl or optionally substituted phenyl,

A represents a group -CH ₂ CH ₂ -,-(CH ₂ ) ₃ -or -CH = CH-,

Z represents cyano or nitro,

Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen,

R ¹ is , R ² is H, R ³ is OCH ₃ , A is -CH ₂ CH _2- , and the compound of general formula (I) wherein Z is NO ₂ is excluded.

Further, according to the present invention the compound of general formula (I)

It has been found that the compounds of the general formula (II) are obtained by reacting with halogen compounds of the general formula (III) in the presence of a base and, optionally, in the presence of a diluent:

Where

R ¹ , R ² , R ³ , A and Z are each as defined above,

X represents halogen (especially chlorine or bromine).

Finally, the novel compounds of general formula (I) have very good biological properties and are particularly effective at controlling animal pests, in particular insects, arachnids and nematodes, which are encountered in the field of protection and hygiene in agriculture, forestry, stored products and materials. Suitable.

Formula (I) provides a general definition of a compound according to the invention.

The range of preferred substituents or radicals listed in the general formulas mentioned above and hereafter is shown below:

R ¹ is preferably fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₂ -alkyl (optionally substituted by fluorine and / or chlorine), C ₁ -C ₂ -alkoxy (fluorine and / or Optionally substituted by chlorine), C ₁ -C ₂ -alkylthio (optionally substituted by fluorine and / or chlorine) or C ₁ -C ₂ -alkylsulfonyl (optionally substituted by fluorine and / or chlorine) Pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl optionally substituted by A 5- to 6-membered heterocyclic group selected from the group consisting of

R ² preferably denotes hydrogen or C ₁ -C ₆ -alkyl,

R ³ preferably represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ ,

From here,

R ⁴ , R ⁵ and R ⁶ are preferably independently of each other 1 to 5 such as C ₁ -C ₁₂ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, fluorine, chlorine and bromine atoms C ₁ -C ₄ -halogenoalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -alkylamino-C ₁ -C ₄ having ₄ same or different halogen atoms -alkyl or di (C ₁ -C ₄₎ alkylamino, -C ₁ -C ₄ - alkyl, or represent, the same or different substituents to be optionally - to tri-substituted C ₃ -C ₆ - cycloalkyl (in which a preferred Substituents may include halogen, C ₁ -C ₄ -alkyl, and C ₁ -C ₄ -halogenoalkyl having 1 to 5 identical or different halogen atoms such as F, Cl and Br atoms). or, respectively, the same or different substituents to be optionally - to tri-substituted phenyl or benzyl (wherein phenyl preferred substituents are halogen at each occurrence, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy Represents a halogeno alkoxy group, and a nitro group) - halogenoalkyl and C ₁ -C ₄ -, and C ₁ -C ₄ having fluorine, chlorine and 1 to 5 identical or different halogen atoms such as bromine atoms in each case, ,

R ⁷ and R ⁸ preferably represent, independently of each other, hydrogen, C ₁ -C ₆ -alkyl or C ₂ -C ₄ -alkenyl, or phenyl or benzyl, mono- to trisubstituted by the same or different substituents, respectively Preferred phenyl substituents here are in each case one to five identical or different halogen atoms, such as halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, and in each case fluorine, chlorine and bromine atoms Having C ₁ -C ₄ -halogenoalkyl and C ₁ -C ₄ -halogenoalkoxy), and

R ⁹ preferably represents C ₁ -C ₄ -alkyl or is phenyl mono- to trisubstituted by the same or different substituents, where possible substituents are halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, and in each case are C ₁ -C ₄ -halogenoalkyl and C ₁ -C ₄ -halogenoalkoxy having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms). ,

A preferably represents a group -CH ₂ CH ₂ -,-(CH ₂ ) ₃ -or -CH = CH-,

Z preferably represents cyano or nitro,

Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen,

R ¹ is , R ² is H, R ³ is OCH ₃ , A is -CH ₂ CH _2- , and the compound of general formula (I) wherein Z is NO ₂ is excluded.

R ¹ particularly preferably represents 6-chloro-3-pyridyl (6-chloro-pyridin-3-yl) or 2-chloro-5-thiazolyl (2-chloro-thiazol-5-yl),

R ² particularly preferably represents hydrogen or C ₁ -C ₅ -alkyl,

R ³ particularly preferably represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ ,

From here,

R ⁴ , R ⁵ and R ⁶ are particularly preferably independently of _one another such as C ₁ -C ₈ -alkyl, C ₁ -C ₂ -alkoxy-C ₁ -C ₂ -alkyl, fluorine, chlorine and bromine atoms; C ₁ -C ₂ -halogenoalkyl, allyl, propargyl, C ₁ -C ₂ -alkylamino-C ₁ -C ₂ -alkyl, di (C ₁ -C ₂ ) alkyl having two identical or different halogen atoms Phenyl or benzyl, which represents amino-C ₁ -C ₂ -alkyl, cyclopropyl, cyclopentyl or cyclohexyl, or is optionally mono- to disubstituted by the same or different substituents, respectively, where possible phenyl substituents are in each case fluorine, Chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy and nitro),

R ⁷ and R ⁸ particularly preferably independently of one another represent hydrogen, C ₁ -C ₄ -alkyl, vinyl or allyl, or each independently phenyl or benzyl optionally substituted by the same or different substituents (where possible Phenyl substituents in each case represent fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy),

R ⁹ particularly preferably represents phenyl or ethyl or is optionally mono- to di-substituted by the same or different substituents, where possible substituents are fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and tri Fluoromethoxy),

A particularly preferably represents a group -CH ₂ CH ₂ -or -CH = CH-,

Z particularly preferably represents cyano or nitro,

Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen,

R ¹ is , R ² is H, R ³ is OCH ₃ , A is -CH ₂ CH _2- , and the compound of general formula (I) wherein Z is NO ₂ is excluded.

Preferred compounds according to the invention are substances of the general formulas (IA) to (ID)

Wherein R ² , R ³ and Z have the general, preferred or particularly preferred meanings mentioned above.

Preferred compounds according to the invention are also represented by the following general formulas (IA-1), (IA-2), (IB-1), (IB-2), (IC-1), (IC-2), (ID- 1) and (ID-2) are:

Wherein R ³ has the general, preferred or particularly preferred meaning mentioned above.

The definitions or explanations of the general or preferred radicals mentioned above apply to the final product and correspondingly to starting materials and intermediates. These radical definitions can be combined with one another as desired, ie they comprise a combination between the respective preferred ranges.

In accordance with the invention preference is given to compounds of the formula (I) which comprise a combination of the meanings mentioned as preferred above.

Particular preference is given to compounds of the formula (I) which comprise according to the invention a combination of the definitions mentioned as particularly preferred above.

In the above and subsequent radical definitions, hydrocarbon chains such as alkyl, including those bonded with heteroatoms such as alkoxy, are in each case as straight or branched as possible.

When 1- (6-chloro-pyridin-3-yl-methyl) -2-nitroimino-imidazolidine and i-propoxymethyl chloride are used as starting materials, the procedure of the process according to the invention is as follows. It can be represented by the same scheme:

Compounds of the general formula (II) which are necessary as starting materials in carrying out the process according to the invention are known (see eg EP-A 0 192 060, EP-A 0 235 725, EP-A 0 259 738 and EP-A). 0 315 826) and / or may be obtained by the methods described herein.

Halogen compounds of the general formula (III) which are also used as starting materials in carrying out the process according to the invention are generally known compounds of organic chemistry and / or can be obtained by generally known methods.

The process according to the invention for preparing novel compounds of general formula (I) is preferably carried out using diluents. Suitable diluents are substantially all inert organic solvents. These are preferably optionally halogenated aliphatic and aromatic hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, Chlorobenzene and o-dichlorobenzene; Ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether, and diglycol dimethyl ether, tetrahydrofuran and dioxane; Ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, ethers such as methyl acetate and ethyl acetate; Nitriles such as acetonitrile and propionitrile; Amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone, and also dimethyl sulfoxide, tetramethylene sulfone and hexamethylphosphate triamide.

Bases that can be used in the method according to the invention are all conventional proton receptors. As these, alkali metal or alkaline earth metal hydroxides, alkali metal or alkaline earth metal hydrides, alkali metal or alkaline earth metal carbonates or bicarbonates, or nitrogen bases are used. These include sodium hydroxide, potassium hydroxide, sodium hydride, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) And diazabicycloundecene may be mentioned.

In the process according to the invention the reaction temperature can vary within a relatively wide range. The reaction is generally carried out at a temperature of -40 to +200 ° C, preferably -10 to 100 ° C.

When carrying out the process according to the invention to prepare compounds of general formula (I), 1 to 3 moles, preferably 1 to 2 moles of halogen of general formula (III) per mole of compound of general formula (II) Compounds are generally used.

Aftertreatment and separation of the final product are carried out in a conventional manner.

The active compounds are suitable for controlling animal pests, especially insects, arachnids and nematodes, encountered in the fields of agriculture, forestry, storage products and materials, and hygiene, and have good crop tolerance and low toxicity to warm-blooded animals. These can preferably be used as crop protection agents. They are active for all or some stages of species and development that are moderately sensitive or resistant. The pests mentioned above include:

The order of Isopoda, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

From the order of Diloplopoda, for example Blaniulus guttulatus.

From the order of Chilopoda, for example, Geophilus carpophagus and Scutigera spec.

From the order of the symphyla, for example Scutigerella immaculata.

From the order of Thysanura, for example, Lepisma saccharina.

The order of Collembola, for example Onychiurus armatus.

From the order of the Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Ah Keta Domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Systoser Cagregaria (Schistocerca gregaria).

From the order of the dermaptera, for example Porficula auricularia.

Termite Isoptera, for example Reticulitermes spp.

Anoplura, for example Pediculus humanus corporis, Haematopinus spp. And Linognathus spp.

Allophaga, for example Trichodectes spp. And Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis and Tripps tabaci.

From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rodney Rhodnius prolixus and Triatoma spp.

The cicada (Homoptera), for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Apis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Apis fabae, Apis pomi, Eriosoma lanigerum, hyaloptherus arun Hyniopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humulli humuli, Rhopalosiphum padi, Empoasca spp., Eucelis bilobatus, Nephotettix cincticeps, Lecanium corni ), Saisetia oleea (Saisset) ia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudo Coscus species (Pseudococcus spp.) And Psylla spp.

The order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Flutella maculipennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. ), Buculatrix thurberiella, Phyloknistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodorf Terra Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo species spp.), Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinnea pelionella pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clichy ambigu Clysia ambiguella, Homona magnanima, and Tortrix viridana.

The order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus , Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp. .), Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antoninomus species (Anthonomus spp.), Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorrinkus assimilus us assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrasno spp., Atenagen spp. ., Lyctus spp., Meligethes aeneus, Pintin spp., Niptus hololeucus, Gibbium psylloides ), Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melonta melolontha, Amphimalon solstitialis and Costelitra zealandica.

Hymenopera species, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa species Vespa spp.).

Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species ( Musca spp.), Pannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. ), Gastrophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp. , Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomina hyosquiami (Pegomyia hyoscyami), Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the tree of Siphonaptera, for example Xenopsylla cheopis and Ceratophyllus spp.

Arachnida, for example Scorpio maurus and Latrodectus mactans.

The order of the species Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriopies libis (Eriophyes ribis), Phyllocoptruta oleivora, Bophillus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. .), Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. ), Bryobia praetiosa, Panonychus spp. And Tetranychus spp.

Plant parasitic nematodes include, for example, Pratylenkus spp., Radopholus similis, Ditylenchus dipsaci, Tylenculus semipenetrans , Heterodera spp., Globoderra spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp. , Xiphinema spp. And Trichodorus spp.

The compounds of formula (I) according to the invention have particularly potent pesticidal activity.

These are leaf and soil insects that damage plants, such as mosquito larvae (Aedes aegypti), black bean aphids (Aphis fabae), and constellation flies (Hilemiya antiquaa). (Hylemyia antiqua) Egg, peach hump aphid (Myzus persicae), cicada locust (Nephotettix cincticeps), mustard beetle (Phaedon cochleariae) )) Larvae and matrix maggots (Spodoptera frugiperda) can be used particularly successfully to control larvae.

The active compounds according to the invention are also root-systemic in function.

The active compounds are solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension emulsion concentrates, and natural and synthetic materials impregnated with the active compounds, and microcapsules in polymeric materials. It may be converted to a conventional formulation such as.

These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers. do.

If the extender used is water, for example an organic solvent can also be used as cosolvent. Suitable liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions, mineral oils and vegetable oils; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide and dimethylsulfoxide, and water.

Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silica, alumina and silicates. Suitable granular carriers for granulation are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husks, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam-forming agents are for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkylsulfonates, Alkylsulfates, arylsulfonates and protein hydrolysates. Suitable dispersants are for example lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and powders such as polyvinyl acetate, natural and synthetic polymers in the form of granules or latex, and natural and synthetic phospholipids such as cephalin and lecithin can be used in the formulation. have. As other additives, mineral oil and vegetable oil may be used.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic dyes such as, for example, alizarin dyes, azo dyes and metal phthalocyanines, and iron, manganese, boron, copper, cobalt, molybdenum and zinc Micronutrients such as salts can also be used.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The active compounds according to the invention are in the form of their commercially available preparations as mixtures with other active compounds such as insecticides, attractants, fungicides, fungicides, acaricides, nematicides, fungicides, growth-modulating substances or herbicides and their It may be present in the form of use prepared from the formulation. Pesticides include, in particular, substances produced by, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and microorganisms.

Examples of particularly advantageous mixing components are as follows:

Fungicides:

Aldimorph, Ampropyl Force, Ampropyl Force Potassium, Andoprim, Anilazine, Azaconazole, Azoxystrobin,

Benalacyl, Benodanil, Benomyl, Benzamacryl, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, Buprimate, Butiobate,

Calcium Polysulfides, Capsaicin, Captapol, Captan, Carbendazim, Carboxin, Carbon, Quinomethionate, Clobenthiazone, Chlorfenazole, Chloronev, Chloropicrine, Chlothalonil, Clozolinate, Chloro Zillacon, cupranev, cymoxanyl, cyproconazole, cyprodinyl, cypropuram,

Devacarb, dichlorophene, diclobutrazole, diclofloanid, diclomezin, dichloran, dietofencarb, difenokonazole, dimethirimol, dimethomorph, dinicoazole, dinicoazole -M, dinocap, diphenylamine, dipyrithione, ditalimphos, dithianon, dodemorph, dodine, drazosolone,

Edifene Force, Epoxyconazole, Etaconazole, Ethirimol, Etridiazole,

Sofasadon, phenafanil, phenarimol, fenbuconazole, fenfuram, phenytropane, fenpiclonyl, phenpropidine, fenpropormorph, fentin acetate, fentin hydroxide, ferbam, perimzone, flua Last, Flumetober, Fluoride, Fluquinconazole, Fluprimidol, Flusilazole, Flusulfamid, Flutolanil, Flutriafol, Polpet, Pocetyl-aluminum, Pocetyl-sodium, Phthalide , Fuberidazole, furlaxyl, furametpyr, furcarbonyl, furconazole, furconazole-cis, purmecyclox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalyl, imibenconazole, iminooctadine, iminooctadine albesylate, iminooctadine triacetate, iodocarb, ifconazole, iprobenfos (IBP), iprodione, irumamycin, isopro Thiolane, isovaledion,

Kasugamycin, cresoxime-methyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures,

Mancoper, Mancozeb, Manev, Meperimzone, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metomeclam, Metsulfobox, Mildiomycin , Michaelrobutanyl, michaelrozoline,

Nickel dimethyldithiocarbamate, nitrotal-isopropyl, noarimol,

Opuras, oxadixyl, oxamocarb, oxolinic acid, oxycarboxime, oxypentin,

Paclobutrazole, pepurazoate, fenconazole, pensicuron, phosphodiphene, fimaricin, piperaline, polyoxine, polyoxolim, probenazole, prochloraz, prosaimidone, propamocarb, Propanosine-sodium, propiconazole, propineb, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxipur,

Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl , Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, triclamid, tricyclazole, tridemorph, trifluzazole, tripolin, triticonazole,

Uniconazole,

Validamycin A, vinclozoline, viniconazole,

Zarylamide, Genev, Zara, and also

Dagger G,

OK-8705,

OK-8801,

α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,

α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,

α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

α- (5-methyl-1,3-dioxan-5-yl) -β-[[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazole-1-ethanol ,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,

(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,

Isopropyl {2-methyl-1-[[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamate,

1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) ethanone O- (phenylmethyl) -oxime,

1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,

1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,

1-[(diiodomethyl) sulfonyl] -4-methylbenzene,

1-[[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,

1-[[2- (4-chlorophenyl) -3-phenyloxyranyl] methyl] -1 H-1,2,4-triazole,

1- [1- [2-[(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1 H-imidazole,

1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide,

2,6-dichloro-5- (methylthio) -4-pyrimidinylthiocyanate,

2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,

2,6-dichloro-N-[[4- (trifluoromethyl) phenyl] methyl] benzamide,

2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,

2-[(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,

2-[[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -aD-glucopyranosyl] amino] -4-methoxy-1 H-pyrrolo [2, 3-d] pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) pentanedinitrile,

2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,

2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,

2-phenylphenol (OPP),

3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,

3,5-dichloro-N- [cyano-[(1-methyl-2-propynyl) oxy] methyl] benzamide,

3- (1,1-dimethylpropyl) -1-oxo-1H-indene-2-carbonitrile,

3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,

4-methyltetrazolo [1,5-a] quinazolin-5 (4H) -one,

8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine,

8-hydroxyquinoline sulfate,

9H-Xanthene-2-[(phenylamino) carbonyl] -9-carboxylic acid hydrazide,

Bis- (1-methylethyl) -3-methyl-4-[(3-methylbenzoyl) oxy] -2,5-thiophendicarboxylate,

Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol,

Cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,

Ethyl [(4-chlorophenyl) azo] cyanoacetate,

Potassium bicarbonate,

Methane tetrathiol sodium salt,

Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,

Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alanineate,

Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alanineate,

N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexanecarboxamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) -acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) -acetamide,

N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitrobenzenesulfonamide,

N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,

N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,

N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,

N- (6-methoxy) -3-pyridinyl-cyclopropanecarboxamide,

N- [2,2,2-trichloro-1-[(chloroacetyl) amino] ethyl] benzamide,

N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxymethaneimideamide,

N-formyl-N-hydroxy-DL-alanine-sodium salt,

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

Spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran-3'-one.

disinfectant:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

Pesticides / Acaricides / Nematicides:

Abamectin, AC 303 630, Acetate, Acrinatrin, Alanicab, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Ajinfoss A, Ajinfoss M, Azocyclo Teen, AKD 1022,

Bacillus thuringiensis, bendiocarb, benfuracarb, benzultope, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocaxine, butylpyridaben ,

Cadusafos, cabaril, cabofuran, cabofennotion, cabosulphan, katop, CGA 157 419, CGA 184 699, cloetocarb, chlorethoxy force, chlorfenbinfos, chlorfluazuron, chlormephos, chlor Pyriphos, Chlorpyriphos M, Cis-Resmethrin, Closightrin, Clofenthezin, Cyanophos, Cycloprotrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazine,

Deltamethrin, Demethone M, Demethone S, Demethone S-methyl, Diaelodene, Diapentiouron, Diazinon, Diclopention, Dichlorbos, Diclifoss, Dicrotophos, Diethion, Diple Rubenzuron, Dimethoate, Dimethylbinforce, Dioxation, Disulfotone,

Edifene force, emamectin, esfen valerate, thiophencarb, ethion, etofenprox, etoprofos, erythropose,

Phenamifos, phenaquinone, fenbutatin oxide, phenythrothione, phenobcarb, phenothiocarb, phenoxycarb, phenpropatrine, fenpyrad, fenpyroximate, pention, fenvalrate, fipro Neil, Fluazinam, Flucycloxonon, Flucytinate, Flufenoxuron, Flufenprox, Fluvalinate, Phonophos, Formotion, Phosthiazate, Pufenfenrox, Furateocarb,

HCH, heptenophos, hexaflumuron, hexthiaxans,

Imidacloprid, ifprobenfoss, isazofoss, isofenfoss, isoprocarb, isoxation, ivermectin,

Lambda-cyhalothrin, lufenuron,

Malathion, Mecarbam, Mevinforce, Mesulfenphos, Metaldehyde, Metacryphos, Metamidophos, Metidathione, Methiocarb, Methomil, Mettolcarb, Milvemectin, Monoclotophos, Moxidecin,

Nal red, NC 184, NI 125, nitenpyram,

Ometoate, oxamyl, oxydemethone M, oxydepropos,

Parathion A, Parathion M, Permethrin, Pentoate, Forate, Posalon, Phosmet, Phosphomidone, Bombardment, Pyrimicarb, Pyrimiphos M, Pyrimiphos A, Propenophos, Promecab, Propa Phos, propoxur, prothiophos, protoate, pymetrozine, pyraclophos, pyridapention, pyresmethrin, pyrethrum, pyridaben, pyrimidipene, pyriproxyfen,

Quinal Force,

RH 5992,

Salitione, cebufoss, silafluorene, sulfotep, sulfpropos,

Tebufenozide, Tebufenpyrad, Tebupyrimifos, Teflubenzuron, Tefluthrin, Temefoss, Terbam, Terbufoss, Tetrachlorbinfos, Thiaphenox, Thiodicarb, Thiophanox, Thiomethone, thionazin, thuringiencin, tralomethrin, triarathene, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb, TI 435,

Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

Other known active compounds, such as herbicides, or mixtures with fertilizers and growth regulators are also possible.

When used as pesticides, the compounds according to the invention can also be present in admixture with synergists, in their commercial preparations and also in the use forms prepared from these preparations. Synergists are compounds that increase the activity of an active compound without having to have activity on its own.

The active compound content of the use forms prepared from commercial formulations can vary within wide ranges. The active compound concentration of the use forms can be 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.

Application is carried out in a manner suitable for the use form.

When used in pests of hygiene pests and stored products, the active compounds show excellent residual activity against wood and clay and excellent stability against alkalis on lime substrates.

The active compounds according to the invention are not only plant, sanitary pests, and stored product pests, but also animal parasites (in vitro parasites) in the field of veterinary medicine, for example, hard mites, mollusks, mites, scabies mites, leaf mites, flies ( Biting and licking), parasitic fly larvae, teeth, hairy teeth, algae teeth and fleas. These parasites include:

Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Pthirus spp. And Soleil Sonopotes spp.

Molophagida and Amblycerina and Ischnocerina subs, such as Trimenopon spp., Menopon spp., Trinoton spp. ), Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., And Felicola spp.

Diptera and Nematotosrina and Brachiycerina subfamily, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Plebotomus spp., Lutzomyia spp., Culicoides spp., Chrysophs Crysops spp., Hibomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philippimia spp. spp.), Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morelia spp., Panni spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp. spp.), come Partia species (Wohlfartia spp.), Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasosterophilus spp., Hippoboska Species (Hyppobosca spp.), Lipoptana spp. And Melophagus spp.

From the order of Siphonaptera, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp. And Ceratophyllus spp.

From the order of Heteroptera, for example Cimex spp., Triatoma spp., Rhodnius spp. And Panstrongylus spp.

The tree of Blatarida, for example, Blata orientalis, Periplaneta americana, Blata germanica and Supela spp.

Acarina (Acarida) subclass and the tree of Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otabius spp ., Ixodes spp., Amblyomma spp., Bophylus spp., Dermancentor spp., Haemaphysalis spp. ), Hyaloma species (Hyalomma spp.), Ripicephalus spp., Dermanisus spp. ), Sternostoma spp. And Varoa spp.

Actinedida (Prostigmata) and Acaridida (Astigmata) necks, for example Acarapis spp., Cheyletiella spp. ), Ornithocheyletia spp., Myobia spp., Sorergates spp., Demodex spp., Trombicula spp. , Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. , Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp. , Notoedres spp., Knemidocoptes spp., Cytodites spp., And Laminosioptes spp. .

The compounds according to the invention show good development-inhibiting activity against, for example, fly larvae of Lucilia cuprina.

The active compounds of formula (I) according to the invention are also useful for agriculturally produced livestock such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese and bees, and It is suitable for controlling pets such as arthropods that invade dogs, cats, birds in fish cages and fish tanks, and also so-called laboratory animals such as hamsters, guinea pigs, rats and mice.

In the field of veterinary medicine, the active compounds according to the invention are for example administered by enteric administration by methods such as tablets, capsules, beverages, potions, granules, pastes, pills, feeds, for example dipping or bathing, spraying By transdermal use in the form of swelling and drips, washing and misting and in the form of shaped articles containing the active compound, for example necklaces, ear marks, tail marks, leg bands, bridles or indicators. It is used in a known manner.

When used in livestock, poultry, pets, etc., the active compounds of general formula (I) are directly as preparations (e.g. powders, emulsions, free-flowing compositions) containing the active compounds in an amount of 1 to 80% by weight. Or it may be diluted to 100 to 10,000 times, or may be used in the form of a chemical bath.

It has also been found that the compounds of the general formula (I) according to the present invention exhibit potent insecticidal action against insects that destroy industrial materials.

The following insects may be mentioned as preferred examples, but are not limited to these:

Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Rick Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Mintes Minthes rugicollis, Zyleborus spp., Tryptodendron spp., Apate monachus, Bostrychus capucins, Heterobostricus Brunne Scotland (Heterobostrychus brunnes), Ceylon sinok species (Synoxylon spp.) And Dino de Luz minu tooth (Dinoderus minutus).

From the necks of Hymenopterans, for example, Sirex jubencus, Urocerus gigas, Urocerus gigas taignus, Uroserus augur ( Urocerus augur).

Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes , Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zotermopsis nevadensis and Coffpe Coptotermes formosanus

Bristletails, for example Lepisma saccharina

Industrial materials in the context of the present invention are understood in the sense of non-living materials, for example plastics, adhesives, sizes, papers and cards, leather, wood and processed wood products, and coating compositions.

Materials that must be very particularly protected against pest infestation are wood and processed wood products.

Wood and processed wood products which may be protected by the preparations or mixtures containing them according to the invention are for example construction wood, wood beams, railway sleepers, bridge components, thighs, wooden vehicles, boxes, It is understood to mean wood products which are very commonly used in pallets, containers, telephone poles, wooden signs, windows and doors made of wood, plywood, chip boards, connectors, or building construction or building connections.

The active compounds can be used on their own in the form of concentrates or common conventional preparations, for example powders, granules, solutions, suspensions, emulsions or pastes.

The mentioned formulations can be prepared by methods known per se, for example, using the active compound in at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, waterproofing agent, optionally drying agent and UV stabilizer and, And dyes and pigments and also other processing aids.

The pesticidal compositions or concentrates used to protect wood and wood products contain the active compounds according to the invention in concentrations of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.

The amount of composition or concentrate used depends on the nature and frequency of the pest and the medium. Optimal use can be determined in each case by a series of tests. In general, however, it is sufficient to use from 0.0001 to 20% by weight of active compound, preferably from 0.001 to 10% by weight, based on the substances to be protected.

The solvents and / or diluents used are organic chemical solvents or solvent mixtures and / or low volatility oily or oily organic chemical solvents or solvent mixtures and / or polar organic chemical solvents or solvent mixtures and / or water, and emulsifiers and / or if appropriate Or humectant.

Preferably, an oily or oily solvent having an evaporation number of at least 35 and a flash point of at least 30 ° C, preferably at least 45 ° C, is used as the organic chemical solvent. Suitable mineral oils or their aromatic fractions, or mixtures of mineral oil-containing solvents, preferably white spirit, petroleum and / or alkylbenzenes, are used as low volatility, water-insoluble oily and oily solvents.

Mineral oil having a boiling range of 170 to 220 ° C, white oil having a boiling range of 170 to 220 ° C, spindle oil having a boiling range of 250 to 350 ° C, petroleum and aromatic compounds having a boiling range of 160 to 280 ° C, terebin ( terpentine) oil and the like are advantageously used.

In a preferred embodiment, high-boiling mixtures of liquid aliphatic hydrocarbons having a boiling range of 180 to 210 ° C. or aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 ° C. and / or spindle oil and / or monochloronaphthalene, preferably Α-monochloronaphthalene is used.

Low volatility organic oily or oily solvents having an evaporation index of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C., the solvent mixture also has a flash point of at least 35 and a flash point of at least 30 ° C., preferably at least 45 ° C. If the pesticide / fungicide mixture can be dissolved or emulsified in this solvent mixture, it may be partially replaced by an intermediate or high volatility organic chemical solvent.

According to a preferred embodiment, an organic chemical solvent or solvent mixture, or part of an aliphatic polar organic chemical solvent or solvent mixture, is replaced. For example, aliphatic organic chemical solvents having hydroxyl and / or ester and / or ether groups such as glycol ethers, esters and the like are preferably used.

The organic chemical binders used within the scope of the present invention are known per se and are synthetic resins and / or combined dry oils, in particular acrylics, which can be diluted with water and / or dissolved, dispersed or emulsified in the organic solvent used. Rate resins, vinyl resins such as polyvinyl acetate, polyester resins, polycondensation or polyaddition resins, polyurethane resins, alkyd resins or modified alkyd resins, phenolic resins, hydrocarbon resins such as indene / coumar Binders consisting of or comprising coumarone resins, silicone resins, dry vegetable oils and / or dry oils and / or natural and / or synthetic resins and which are physically dried binders.

Synthetic resins used as binders can be used in the form of emulsions, dispersions or solutions. Up to 10% by weight bitumen or bituminous material may also be used as the binder. In addition, dyes, pigments, waterproofing agents, odor masking agents and inhibitors or corrosion inhibitors known per se may further be used.

According to the invention, compositions or concentrates containing at least one alkyd resin or modified alkyd resin and / or dry vegetable oil as organic chemical binders are preferred. Alkyd resins having an oil content of at least 45% by weight and preferably from 50 to 68% by weight are preferably used according to the invention.

All or part of the above mentioned binders may be replaced with fixatives (mixtures) or plasticizers (mixtures). These additives are used to prevent evaporation and crystallization or precipitation of the active compounds. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

Plasticizers include phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, From the chemical groups of stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid esters Induced.

The fixative is chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether, or ketones such as benzophenone or ethylene benzophenone.

If desired, water mixed with one or more of the aforementioned organic chemical solvents or diluents, emulsifiers and dispersants is also possible as a solvent or diluent.

Wood is particularly effectively preserved by large scale industrial injection methods, for example by vacuum, double vacuum or compression treatment.

Ready-to-use compositions may also optionally contain other pesticides and, if appropriate, also one or more fungicides.

Possible further mixing components are preferably the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in this document are clearly components of the present application.

Particularly preferred mixed ingredients are insecticides such as chlorpyriphos, bombard, silafluorine, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, Hexaflumuron and triflumuron, and also fungicides, for example epoxyconazole, hexaconazole, azaconazole, propicosol, tebuconazole, cyproconazole, metconazole, imazaryl, diconazole Chlorfluanid, tolylufluoride, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazoline-3- It's on.

Examples of preparation and use of the active compounds according to the invention are illustrated by the following examples.

Example

Example 1

At 5 ° C., 1.5 g (0.0063 mol) of 1- (6-chloro-pyridin-3-yl-methyl) -2-cyanoiminoimidazolidine in 25 ml of anhydrous dimethylformamide was diluted with 0.25 g (0.0063 mol) of sodium hydride. And a small amount of stirring. After stirring for 1 hour at room temperature, 0.7 mL (0.0063 mol) of i-propoxymethyl chloride was added at 0 ° C. and the mixture was stirred overnight. The solvent was distilled off to concentrate the reaction mixture and the residue was dissolved in petroleum ether and then filtered. The filtrate was purified by silica gel column chromatography (methylene chloride / methanol 15 / 0.5).

0.57 g (29% of theory) of 1- (6-chloro-pyridin-3-yl-methyl) -2-cyanoimino-3-i-propoxymethyl-imidazolidine having a melting point of 85 to 87 ° C It was.

Example 2

1.5 g (5.7 mmol) of 1- (2-chloro-thiazol-5-yl-methyl) -2-nitroiminoimidazolidine in 5 ml of anhydrous dimethylformamide was added in small amounts with 0.26 g (6.5 mmol) of sodium hydride. Mix with stirring. The mixture was stirred briefly at room temperature, then 0.7 g (6.5 mmol) of n-propoxymethyl chloride was added while cooling and the mixture was stirred overnight. The reaction mixture was concentrated under reduced pressure and the residue was mixed with water and then extracted with methylene chloride. The organic phase was dried over sodium sulphate and concentrated, then the residue was stirred with diisopropyl ether and then concentrated again.

1.54 g of 1- (2-chloro-thiazol-5-yl-methyl) -2-nitromino-3-n-propoxymethyl-imidazolidine with calculated index n ²⁰ _D = 1.5781 (76% of theory) ) Was obtained.

Example 3

At room temperature, 2.54 g (0.01 mol) of 1- (6-chloro-pyridin-3-yl-methyl) -2-nitroiminoimidazolidine in 10 ml of anhydrous dimethylformamide was added with 0.44 g (0.011 mol) of sodium hydride. Mix in small portions. After the mixture was stirred briefly, 2.17 g (0.0215 mol) of bromoethoxymethyl chloride was added while cooling and the mixture was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure and the residue was mixed with water and then extracted with methylene chloride. The organic phase was dried over sodium sulphate and concentrated, then the residue was stirred with diisopropyl ether and then filtered. The filtrate was purified by silica gel column chromatography (methylene chloride / methanol 10/1).

2.3 g (53% of theory) of 1- (6-chloro-pyridin-3-yl) -2-nitroimino-3-bromoethoxymethyl-imidazolidine having a melting point of 90 to 92 ° C were obtained.

Similarly to Preparation Examples 1-3, and according to the general description for the preparation of compounds of general formula (I), the compounds shown in Table 1 below were obtained:

Table 1

[logP = logP values were determined by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid) according to EEC directive 79/831 Annex V. A8.

Example of use

Example A

Aedes Exam

Solvent: 1000 parts by weight of methanol

1 part by weight of the active compound is mixed with the specified amount of solvent and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Mosquito larvae (Aedes aegypti) were placed in the active compound formulation at the desired concentration.

After a certain period of time, the effect on the larvae was determined. 100% means that all animals have had severe symptoms or have died; 0% means that none of the animals have been killed.

In this test, the compounds of Preparation Examples 4, 5 and 7 exhibited 100% rescue after 4 hours at typical active compound concentrations of 0.0016% in each case.

Example B

Apis Test (systemic action)

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Soybean plants (vicia fabae) heavily infected with black soybean aphid (Apis favae) were irrigated so that in each case 20 ml of the active compound formulation of the desired concentration was penetrated into the soil without wetting the branches. It was. The active compound is absorbed into the roots and delivered to the branches.

After a certain period of time, the percent rescued was determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed.

In this test, the compounds of Preparation Examples 4 and 9, and the compounds of Preparation Example 5 exhibited a rescue rate of 100% and 95% respectively after 4 days at a typical active compound concentration of 0.01% in each case.

Example C

Hillime test

Solvent: 100 parts by weight of acetone

1900 parts by weight of methanol

One part by weight of the active compound is mixed with the specified amount of solvent and the concentrate is diluted with methanol to the desired concentration to prepare a suitable formulation of the active compound.

Specified amounts of the active compound formulation of the desired concentration were pipetted onto standardized amounts of artificial feed. After evaporating the methanol, about 20 eggs of the constellation fly (Hilemiya antiqua) were placed on the feed.

After a certain period of time, the percent control of eggs or larvae was determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.

In this test, the compound of Preparation Example 4 showed a 100% rescue after 7 days at a typical active compound concentration of 0.05%.

Example D

Miss Juice Test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brasica oleracea) heavily infected with peach aphids (Misso Pacifica) were treated by dipping into active compound formulations of the desired concentration.

After a certain period of time, the percent rescued was determined. 100% means that all the aphids have been killed; 0% means that none of the aphids have been killed.

In this test, the compounds of Preparation Examples 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 25 and 36 were 100% rescued after 6 days at typical active compound concentrations of 0.1% in each case. The rate is shown.

Example E

Nepotetics test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Rice hair (Oryzae sativa) was treated by immersion in the active compound formulation of the desired concentration, and infected with cicada larvae (nepotetics synthiceps larva) while the hair was moist.

After a certain period of time, the percent rescued was determined. 100% means that all cicadas have been killed; 0% means that none of the cicadas have been killed.

In this test, compounds of Preparation Examples 4, 10, 12, 13, 14, 15, 18, 19, 21, 24, 25, 26, 33 and 36 were in each case after 6 days at a typical active compound concentration of 0.1% A rescue rate of 100% was shown.

Example F

Phaedon Larva Test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brassica oleracea) were treated by immersion in the active compound formulation at the desired concentration, and infected with mustard beetle larvae (Phaedon cocleariae) while the leaves were damp.

After a certain period of time, the percent rescued was determined. 100% means that all the scarab larvae have been killed; 0% means that none of the scarab larvae have been killed.

In this test, compounds of Preparation Examples 4, 10, 12, 17, 18, 19, 21, 25, 33, 34, 35, and 36 were 100% rescued after 7 days at typical active compound concentrations of 0.1% in each case. The rate is shown.

Example G

Spodoptera prugiferda test

Solvent: Dimethylformamide 7 parts by weight

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Cabbage leaves (Brassica oleracea) were treated by immersion in the active compound formulation at the desired concentration, and infected with owlet moth (Spodoftera prugiferda) larva while the leaves were damp.

After a certain period of time, the percent rescued was determined. 100% means that all the larvae have been killed; 0% means that none of the larvae have been killed.

In this test, compounds of Preparation Examples 2, 10, 12, 13, 17, 18, 20, 25, 33, 35, and 36 had a 100% rescue rate after 7 days at typical active compound concentrations of 0.1% in each case. Indicated.

Example H

Spodoptera prugiferda test / artificial feed

Solvent: 100 parts by weight of acetone

1900 parts by weight of methanol

One part by weight of the active compound is mixed with the specified amount of solvent and the concentrate is diluted with methanol to the desired concentration to prepare a suitable formulation of the active compound.

Specified amounts of the active compound formulation of the desired concentration were pipetted onto standardized amounts of artificial feed. After evaporating the methanol, in each case one owl moth (Spodoftera pruperferda) larvae (L ₂ -L ₃ ) were introduced three times over the feed.

After a certain period of time, the percent rescued was determined. 100% means that all animals have been killed; 0% means that none of the animals have been killed.

In this test, the compound of Preparation Example 4 showed a 100% rescue after 7 days at a typical active compound concentration of 0.05%.

Example I

Critical concentration test / root-systemic action

Test Insect: Apis Pava

Solvent: 4 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the specified amount of solvent and the specified amount of emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

The active compound preparation was mixed well with the soil. The concentration of active compound in the formulation is of no practical importance, only the weight of active compound per soil volume given in ppm (= mg / L) is critical. The treated soil was transferred to pots and planted with pre-germinated peaches. The active compound can thus be absorbed from the soil into the roots of the plant and transferred to the leaves.

To demonstrate the root-systemic effect, after 7 days the leaves were infected with the test animals mentioned above. After 6 days, the number of dead animals was counted or measured. Root-systemic function of the active compound was inferred from the number of dead animals. 100% means that all test animals have died and 0% means that the number of surviving test insects is the same as that of the untreated control.

In this test, the compounds of Preparation Examples 4 and 5 each exhibited a 100% rescue at a typical active compound concentration of 20 ppm.

Example J

Black fly larva test / development activity

Test Animal: Lucilia Cuprina Larva

Solvent: Dimethyl Sulfoxide

20 mg of the active compound was dissolved in 1 ml of dimethyl sulfoxide and diluted with distilled water to further dilute the concentration.

About 20 Lucilia cuprina larvae were introduced into a test tube containing about 1 cm ³ of horse meat and 0.5 ml of the active compound formulation to be tested. After 24 and 48 hours, the effectiveness of the active compound preparations was investigated. Test tubes were transferred to a beaker with sand on the floor. Two days later, the test tube was removed and the pupa was counted.

After 1.5 times the developmental period of the untreated control, the effects of the active compound preparations were evaluated with hatched fly water. 100% means that none are hatched into flies; 0% means that all flies hatch normally.

In this test, the compounds of Preparation Examples 9, 10, 11, 12 and 13 showed a 100% development-inhibitory effect at a typical active compound concentration of 100 ppm.

Claims (7)

Compound of Formula (I): Where R ¹ is a heteroatom ring member containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms (where the number of heteroatoms is 1, 2, 3 or 4), Halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkyl Thio, alkenylthio, halogenoalkenylthio, alkynylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, arylthio, A 5- or 6-membered heterocyclic group optionally substituted by arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and / or alkoxycarbonyl , R ² represents hydrogen or alkyl, R ³ represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ , From here, R ⁴ , R ⁵ and R ⁶ are independently of each other alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkynyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl, or in each case optionally substituted phenyl Or benzyl, R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, or in each case optionally substituted phenyl or benzyl, R ⁹ represents alkyl or optionally substituted phenyl, A represents a group -CH ₂ CH ₂ -,-(CH ₂ ) ₃ -or -CH = CH-, Z represents cyano or nitro, Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen, R ¹ is , R ² is H, R ³ is OCH ₃ , A is -CH ₂ CH _2- , and the compound of general formula (I) wherein Z is NO ₂ is excluded. A compound of formula (I) according to claim 1 characterized by reacting a compound of formula (II) with a halogen compound of formula (III) in the presence of a base and optionally in the presence of a diluent How to manufacture: Where R ¹ is a heteroatom ring member containing 1, 2, 3 or 4 nitrogen atoms and / or one or two oxygen or sulfur atoms (where the number of heteroatoms is 1, 2, 3 or 4), Halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkynyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkynyloxy, alkylthio, halogenoalkyl Thio, alkenylthio, halogenoalkenylthio, alkynylthio, alkylsulfinyl, halogenoalkylsulfinyl, alkylsulfonyl, halogenoalkylsulfonyl, amino, alkylamino, dialkylamino, aryl, arylthio, 5- or 6-membered heterocyclic group optionally substituted by arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and / or alkoxycarbonyl, R ² represents hydrogen or alkyl, R ³ represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ , From here, R ⁴ , R ⁵ and R ⁶ are independently of each other alkyl, alkoxyalkyl, halogenoalkyl, alkenyl, alkynyl, alkylaminoalkyl, dialkylaminoalkyl, optionally substituted cycloalkyl, or in each case optionally substituted phenyl Or benzyl, R ⁷ and R ⁸ independently of one another represent hydrogen, alkyl, alkenyl, or in each case optionally substituted phenyl or benzyl, R ⁹ represents alkyl or optionally substituted phenyl, A represents a group -CH ₂ CH ₂ -,-(CH ₂ ) ₃ -or -CH = CH-, Z represents cyano or nitro, Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen, R ¹ is , R ² is H, R ³ is OCH ₃ , A is -CH ₂ CH ₂ -and the compound of formula (I) wherein Z is NO ₂ is excluded, X represents halogen (especially chlorine or bromine). The method of claim 1, R ¹ is fluorine, chlorine, bromine, cyano, nitro, C ₁ -C ₂ -alkyl (optionally substituted by fluorine and / or chlorine), C ₁ -C ₂ -alkoxy (by fluorine and / or chlorine) Optionally substituted), optionally substituted by C ₁ -C ₂ -alkylthio (optionally substituted by fluorine and / or chlorine) or C ₁ -C ₂ -alkylsulfonyl (optionally substituted by fluorine and / or chlorine) Group consisting of substituted pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl and pyrimidinyl A 5- to 6-membered heterocyclic group selected from R ² represents hydrogen or C ₁ -C ₆ -alkyl, R ³ represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ , From here, R ⁴ , R ⁵ and R ⁶ are independently of each other 1 to 5 identical or equal to C ₁ -C ₁₂ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, fluorine, chlorine and bromine atoms or C ₁ -C ₄ -halogenoalkyl, C ₂ -C ₄ -alkenyl, C ₂ -C ₄ -alkynyl, C ₁ -C ₄ -alkylamino-C ₁ -C ₄ -alkyl having different halogen atoms or C ₃ -C ₆ -cycloalkyl, which represents di (C ₁ -C ₄ ) alkylamino-C ₁ -C ₄ -alkyl or is optionally mono- to trisubstituted by the same or different substituents Halogen, C ₁ -C ₄ -alkyl, and C ₁ -C ₄ -halogenoalkyl having 1 to 5 identical or different halogen atoms such as F, Cl and Br atoms may be mentioned), respectively be optionally substituted by identical or different substituents-to tri-substituted phenyl or benzyl (the phenyl substituents possible here is halogen, C ₁ -C ₄ in each case alkoxy, and each occurrence -alkyl, C ₁ -C ₄ Represents a halogeno alkoxy group, and a nitro group), - having a cow, goat, and 1 to 5 identical or different halogen atoms such as bromine atom, C ₁ -C ₄ - halogenoalkyl and C ₁ -C ₄ R ⁷ and R ⁸ independently of one another represent hydrogen, C ₁ -C ₆ -alkyl or C ₂ -C ₄ -alkenyl, or phenyl or benzyl, each of which is mono- to trisubstituted by the same or different substituents, wherein Possible phenyl substituents are in each case halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, and in each case C ₁ having 1 to 5 identical or different halogen atoms such as fluorine, chlorine and bromine atoms -C ₄ -halogenoalkyl and C ₁ -C ₄ -halogenoalkoxy), R ⁹ represents C ₁ -C ₄ -alkyl or is phenyl mono- to trisubstituted by the same or different substituents, where possible substituents are halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy And in each case are C ₁ -C ₄ -halogenoalkyl and C ₁ -C ₄ -halogenoalkoxy having 1 to 5 identical or different halogen atoms such as fluorine, chlorine and bromine atoms), A represents a group -CH ₂ CH ₂ -,-(CH ₂ ) ₃ -or -CH = CH-, Z represents cyano or nitro, Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen, R ¹ is And R ² is H, R ³ is OCH ₃ , A is —CH ₂ CH ₂ —, and the compound of formula (I) wherein Z is NO ₂ is excluded. The method of claim 1, R ¹ represents 6-chloro-3-pyridyl (6-chloro-pyridin-3-yl) or 2-chloro-5-thiazolyl (2-chloro-thiazol-5-yl), R ² represents hydrogen or C ₁ -C ₅ -alkyl, R ³ represents a group -OR ⁴ , -OCOR ⁵ , -OCOOR ⁶ , -OCONR ⁷ R ⁸ or -OSO ₂ R ⁹ , From here, R ⁴ , R ⁵ and R ⁶ are independently of each other one to two identical or equal to C ₁ -C ₈ -alkyl, C ₁ -C ₂ -alkoxy-C ₁ -C ₂ -alkyl, fluorine, chlorine and bromine atoms or C ₁ -C ₂ -halogenoalkyl, allyl, propargyl, C ₁ -C ₂ -alkylamino-C ₁ -C ₂ -alkyl, di (C ₁ -C ₂ ) alkylamino-C ₁ having different halogen atoms Phenyl or benzyl, which represents one of -C ₂ -alkyl, cyclopropyl, cyclopentyl, or cyclohexyl, or optionally one- to di-substituted, respectively, by the same or different substituents (where possible phenyl substituents are in each case fluorine, chlorine, bromine, Methyl, methoxy, trifluoromethyl, trifluoromethoxy and nitro), R ⁷ and R ⁸ independently of one another represent hydrogen, C ₁ -C ₄ -alkyl, vinyl or allyl, or each independently phenyl or benzyl optionally substituted by the same or different substituents (where possible phenyl substituents are each Fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy), R ⁹ represents methyl or ethyl, or optionally mono- to di-substituted by the same or different substituents, where possible substituents are fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy ), A represents a group -CH ₂ CH ₂ -or -CH = CH-, Z represents cyano or nitro, Provided that when Z represents NO ₂ and A represents -CH ₂ CH _2- , the radical R ² represents hydrogen, R ¹ is And R ² is H, R ³ is OCH ₃ , A is —CH ₂ CH ₂ —, and the compound of formula (I) wherein Z is NO ₂ is excluded. A composition for controlling animal pests, characterized in that it contains at least one compound of formula (I) according to claim 1. Use of a compound of formula (I) according to claim 1 for controlling animal pests. A method of preparing a composition for controlling animal pests, characterized in that the compound of formula (I) according to claim 1 is mixed with a diluent and / or a surfactant.